5-methoxy-imidazo[1,2-a]quinolin-2-carboxaldehyde | 84357-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methoxy-imidazo[1,2-a]quinolin-2-carboxaldehyde
• 英文别名: 5-Methoxyimidazo[1,2-a]quinolin-2-carboxaldehyde；5-methoxyimidazo[1,2-a]quinoline-2-carbaldehyde
• CAS: 84357-17-5
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: XMUQHOMXCSZXLN-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-imidazo[1,2-a]quinolin-2-carboxaldehyde 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 17.0h， 生成 (5-Methoxy-imidazo[1,2-a]quinolin-2-yl)-p-tolyl-methanone
  参考文献：
  名称：

  (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics

  摘要：

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.

  DOI：

  10.1021/jm00401a025
• 作为产物：
  描述：

  5-methoxy-imidazo[1,2-a]quinoline-2-methanol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以75%的产率得到5-methoxy-imidazo[1,2-a]quinolin-2-carboxaldehyde
  参考文献：
  名称：

  (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics

  摘要：

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.

  DOI：

  10.1021/jm00401a025

文献信息

• Imidazo[1,2-a]quinoline derivatives useful as anxiolytics
  申请人：Roussel Uclaf

  公开号：US04387098A1

  公开（公告）日：1983-06-07

  Novel imidazo[1,2-a]quinolines of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, thienyl, pyridyl and phenyl optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms and alkoxy of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 8 carbon atoms,s cyclohexyl, --NO.sub.2 and phenoxy, R.sub.3 is selected from the group consisting of alkoxy and alkylthio of 1 to 8 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable anxiolytic activity and a hypnotic activity and their preparation.

  这是一种新型咪唑[1,2-a]喹啉类化合物，其化学式为##STR1##其中R选择自1至8个碳原子的烷基、噻吩基、吡啶基和苯基，该苯基可选地被卤素、1至5个碳原子的烷基和1至5个碳原子的烷氧基中的至少一种置换；R.sub.1和R.sub.2分别选择自氢、卤素、1至8个碳原子的烷基和烷氧基、环己基、--NO.sub.2和苯氧基中的一种；R.sub.3选择自1至8个碳原子的烷氧基和烷硫基，以及它们的非毒性、药学上可接受的酸盐，具有显著的抗焦虑和催眠活性，且具有制备方法。
• ROBSON, P. A.;BARNES, A. C.
  作者：ROBSON, P. A.、BARNES, A. C.

  DOI：——

  日期：——
• CLEMENTS-JEWERY, STEPHEN;DANSWAN, GEOFFREY;GARDNER, COLIN R.;MATHARU, SAR+, J. MED. CHEM., 31,(1988) N 6, 1220-1226
  作者：CLEMENTS-JEWERY, STEPHEN、DANSWAN, GEOFFREY、GARDNER, COLIN R.、MATHARU, SAR+

  DOI：——

  日期：——
• Dérivés de l'imidazo(1,2-a)quinoléines
  申请人：ROUSSEL-UCLAF

  公开号：EP0062580B1

  公开（公告）日：1985-11-06
• US4387098A
  申请人：——

  公开号：US4387098A

  公开（公告）日：1983-06-07